Phenol, 2-(2-propenyloxy)- → (2R)-3-(o-Allyloxyphenoxy)-1,2-epoxypropane

HRID 1107054

반응식

HRID 1107054 반응식
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])[CH:2]=[CH2:3].[F-].[K+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N+](C1C=C(S(O[CH2:45][C@H:46]2[O:48][CH2:47]2)(=O)=O)C=CC=1)([O-])=O>C1COCC1.O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:45][C@@H:46]1[O:48][CH2:47]1)[CH:2]=[CH2:3]

참가 물질

7

반응물 4

HCID 70772Phenol, 2-(2-propenyloxy)-HCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 522689Potassium FluorideHCID 2724141Tetrabutylammonium Fluoride

생성물 1

HCID 40428630(2R)-3-(o-Allyloxyphenoxy)-1,2-epoxypropane수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

o-Allyloxyphenol (1.0 g) was dissolved in THF (10 ml) under nitrogen atmosphere and the solution was cooled to 0° C. Potassium fluoride (1.55 g) and tetrabutyl ammonium fluoride (0.2 g) were added thereto and the mixture was stirred for 1 hour. Then (S)-glycidyl M-nitrobenzenesulfonate (1.73 g, 99.3% e.e.) was added thereto and the mixture was stirred for 40 hours at the same temperature. After the reaction water was added to the mixture, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/ethyl acetate; 3:2) to give 0.96 g of (R)-3-(o-allyloxyphenoxy)-1,2-epoxypropane (yield 70%, optical purity 95.9% e.e.) as a colorless oil.

후처리

  1. stirringthe mixture was stirred for 40 hours at the same temperature
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate, condensed

출처 및 근거

ORD 기록
ord-11b7878206174909a359773aa0385284
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057476

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